1,1',1''-(Chlorosilylidyne)tris(benzene) → (9H-Fluoren-9-yl)(triphenyl)silane

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Reaction Steps

To a solution of 17 g of fluorene (102.4 mmol) in 300 mL of dry ether was added 46 mL of 2.3M n-butyllithium dropwise over a period of 20 minutes. The mixture was refluxed for 3 hours, cooled in an ice bath, and treated in one portion with a solution of 24 g (81.46 mmol) of triphenylsilyl chloride in 100 mL of dry benzene. The mixture was refluxed for 24 hours, cooled to room temperature, and washed with sat'd NH4Cl (100 mL), brine (150 mL), and water (150 mL). The organic layer was dried over MgSO4 and the solvent was evaporated in vacuo to give a yellow residue which was triturated with methanol to afford 34.18 g (98.9%) of the crude silane as an off-white solid. Recrystallization from EtOAc--EtOH (4:1) gave 27.46 g (79.5%) of the pure triphenylsilane as white needles, m.p. 182°-193° C.; 1H NMR (CDCl3): δ 4.72 (s, 1H, CH), 6.82-7.90 (m, 23H, aryl).

Provenance & Evidence